


Ash's Best Catch

by DraceDomino



Category: Pocket Monsters | Pokemon - All Media Types
Genre: Breeding, Creampie, F/M, Master/Slave, Mindbreak, Rape/Non-con Elements, Rough Oral Sex, Rough Sex
Language: English
Status: Completed
Published: 2017-10-06
Updated: 2017-12-17
Packaged: 2019-01-09 14:07:19
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 2
Words: 7,941
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12278115
Author URL: https://archiveofourown.org/users/DraceDomino/pseuds/DraceDomino
Summary: Fed up with Jessie's constant attempts to steal Pikachu, Ash finally snaps and puts her in her place. It's exactly what you think it is.





	1. Chapter 1

Ash’s Best Catch  
-By Drace Domino

“Good job, Pikachu, that sure put the stupid slut in her place.” Ash growled, tightening a fist as he stepped up to the edge of the battlefield. All of Jessie’s Pokemon had been exhausted and now the Team Rocket girl was there on her knees; trembling and weary from a particularly hard electric shock from Pikachu. As she twitched and tried to bring herself to her hands and knees on the soft grass of the forest, Ash’s voice spoke out again with an angry tone. Clearly, something inside of him was different. Clearly, they had finally pushed him too far. “Don’t try getting up, whore, or I’ll just have Pikachu shock you right back into the ground again.”

“Pika~” Pikachu’s adorable voice followed the threat, and Jessie forced her head to face forward. With her body still crackling from Pikachu’s attack, she looked up at the figure that now towered above her. Ash’s face was veiled by the brim of his hat and his mouth wore an angry scowl; exposing his teeth in predatory fashion while his fists balled tight and furiously. His shoulders trembled from frustration and anger, and before Jessie could squeak out an apology Ash finally spoke up again in his enraged tone.

“I’ve had it with you! I’ve had it with you always chasing me! Always bothering me!” He growled, and as he did so one of his hands dropped down into Jessie’s long, sweeping tail of red hair. The Team Rocket girl gasped as her head was suddenly pulled forward to crash into Ash’s lap, and with trembling eyes she looked at a heavy bulge that was forming from behind the denim of his jeans. He forced his hands to the back of her head, made her rub her face in his crotch, and as he ground his throbbing erection against the villain’s face he continued with his angry tirade. “I could’ve gotten so much pussy by now if it wasn’t for you always interrupting! Misty! Dawn! May! I could’ve had any one of those cunts wrapped around my cock, but nooooo, you and that goddamned sidekick of yours always had to drop in and ruin things!”

“Wha...what…” Jessie’s voice only barely managed to squeak out as she looked up at him, trying her best to press away from his lap. Never had she heard Ash talk to her or anyone else like this, but then...they had never been alone together before. Was this the hard, angry side that he was hiding from everyone? With James and Meowth on the other end of the forest trying to attack Ash’s friends, there was nobody she could call for help. All of her Pokemon were lying dormant in their balls, and Ash was surprisingly strong as he took even tighter fistfuls of her hair. “A...Ash...s...stop it…!”

“No! I won’t fucking stop it!” Ash’s voice snapped back, and he wrenched Jessie’s hair back with a fierce fist. As he forced her head to arch backwards he spit squarely in the slut’s face; watching with delight as it oozed down her cheek and along her slender throat. A wicked smile spread across his features, and he slapped the girl’s cheek hard enough to leave a bright red impact before continuing. “Here’s how it’s going to be, whore. You’re going to open up and suck my cock...and you’re going to make me forget all about those other little sluts I could’ve fucked along the way. And if you refuse?”

“Piiiiiika….!” Pikachu’s threat was immediate, his cheeks flaring with sparks that suggested Jessie would be sent far over the horizon if she dared to say no. With a trembling whimper the villain’s hands pushed again at Ash’s lap, though she was only able to bring herself a few inches away before he slapped her, once more, even harder than before. Her cry carried over the forest for nobody but the Pokemon to hear, and as Ash flexed his fingers and prepared for another slap, Jessie finally gave a tiny, dismal nod.

“A...All right…” She sniffled, and her shoulders gave a weak, pathetic slump. Apparently this was the end of her life of crime; she had been beaten and there was no going back to the way things were. If she behaved herself and did what Ash said she could always quit Team Rocket and leave, and hope to forget about what had happened. With tears already forming in the corners of her eyes she looked up at Ash, and slowly opened up her mouth as if to invite his cock inside. What she received; as her lips parted and her tongue stretched out, was Ash’s spit squarely on her tongue and yet another slap across her increasingly reddening cheeks.

“Whores don’t suck cock while they’re fully dressed.” Ash corrected her with a smirk, and gestured to the uniform she was wearing. “Take the clothes. Throw them in the fucking river.” Nearby a river was moving quickly; so quickly that it was guaranteed to send her clothes immediately downstream. With the increasing knowledge that her submission and humiliation would be a long and sordid affair Jessie nodded and stood to her feet, whimpering as she prepared to do exactly as Ash asked.

She slinked out of her skirt and her blouse, and along with it the panties and bra that had been supplied by Team Rocket. When she turned around she was wearing only the most tantalizing parts of her outfit; knee high leather boots and matching gloves that went past her elbows. She stood alongside the stream and with one tiny sob sent her clothes into the water just as she had been told; watching as they immediately travelled swiftly around the bend and out of sight. Now that she was exposed Ash stepped up close behind her, his hands moving around her body to grope at those lovely, large breasts she had been hiding all this time.

“Bigger tits than I expected you to have.” Ash grinned, grinding his cock against Jessie’s ass through the fabric of his pants. “Bet everyone will be surprised to see when you walk back into town like this, whore. Are you ready to suck?”

Jessie, with full tears now rolling down the sides of her face, gave a tiny nod of forced consent. As soon as she did so Ash gave a triumphant laugh, and his head turned to the side to look to where Pikachu was still waiting for the call to action. He gave the little electric mouse a simple wave, just before he pulled Jessie by the tail of her long red hair once more.

“Pikachu, go keep an eye out. I’ll be fucking damned if I’m interrupted getting a piece of ass this time.”

“Pika pi!” The response was short and efficient, and just a few seconds later Pikachu bounced away to leave them alone. As Ash drug Jessie back towards the grass he wrenched her hair down; forcing her to her knees once more and listening to the gentle sobs coming from her. She was already weak and broken - a stark contrast from her egotistical and villainous persona that she so often wore. The sight of her running mascara and the quivering of her naked body was enough to make Ash throb with an even greater force, and he moved a free hand down to the edge of his zipper.

“I’m not taking any chances with you, cunt.” He growled, just as the denim opened up and he fished out the length of his cock. “I’ll do all the work. All you have to do is open your fuckhole mouth, and don’t pass out.” His smile was cruel, far crueler than Jessie had ever imagined Ash could look. “Good luck on that one...I don’t plan on letting you up for air.”

And with that, Ash unceremoniously exposed his cock and forced Jessie’s mouth squarely down on top of it. It was far larger than the Team Rocket girl ever would’ve suspected, and on the very first thrust Ash forced it right down into her throat. His hands were locked at her hair at the sides of her head, and when he slammed her mouth down against his cock and bashed her nose into her lap he made sure to hold it there for a long, hungry moment. A predatory growl roared through the young man as Jessie instantly started to struggle, pressing her hands to Ash’s lap and trying to force herself away. Her throat bulged with cock, the sides of her mouth drooled lines of spit that matched the path of her tears, and her nearly-naked form scrambled on the grass. The taste of his prick filled her senses, and she was utter unable to pull away as he forced her to hold down into his lap.

“That’s it, slut, fight it all you want.” Ash smirked, his devilish grin flashing even further to the point of madness. “If you get tired out, you’ll just put up less of a fight when I go for your cunt.”

Words that shocked and frightened Jessie down to her core were just enough to keep her distracted - distracted enough so that Ash could start to violently facefuck the older girl. His hips rocked back before slamming forward and his fingers tightened within her hair, battering his prick back and forth and making her throat bulge from the impressively large sculpt of it. Jessie’s voice could finally be heard in the air but only in the form of strangled gasps and gurgles; the noises of a bitch being sloppily facefucked. Spit sputtered from her lips and drooled across her breasts, dark lines trailed her eyes from her rapidly running mascara, and try as she might to push away from Ash the young man firmly had the upper hand. This was happening, and there was nothing she could do to stop it.

Ash groaned in abject primal lust as he took all of his frustrations out on Jessie’s mouth, rocking wildly back only to slam himself in with every ounce of strength. She had caused him and his friends no end of trouble over the years, and this was a sweet reward for putting up with all of her shit. Hearing her gurgling whimpers, feeling her trembling throat try desperately to wrap around his cock, listening to her frequent noises of wailing sobs...it was all a rich pleasure for the young man to enjoy. One hand tightened his fingers into Jessie’s hair while the other held his shaft at the base, and he afforded her a few brief seconds to catch her breath while he pulled his cock out of her throat. While her face remained a spit and slime covered mess Ash slapped her back and forth with that heavy meat, only bringing a higher pitch to her sobs as he spoke out in that same dominant tone.

“Isn’t this so much better than Pikachu sending your whore ass over the horizon?” He grinned in triumph, and forced her head back so he could spit on her once more, this time squarely at the bridge of her nose. As it slide down across one of her closed eyes his cock moved over it, wiping it away and smearing it across the rest of her face. Once his tip lined up against her lips again he was ready to force himself down her throat anew, and he did just that with a thrust that left his balls slapping the soft, tender flesh under her chin. “Probably still not as tight as Misty’s cunt would’ve been, but I’ll take what I can get!”

From there, Jessie was utterly helpless as she allowed herself to be violently throatfucked. Her boots and gloves were pressed to the ground as she rested there on the grass, lines of spit cascading down her body to make her glisten in the afternoon sun. Her tears continued and her jaw ached from keeping her mouth stretched open so wide, but she knew that if she closed it she’d only be punished further. She did the only thing that was within her power - to be a complacent cocksleeve for her long time enemy, letting him have free reign of her mouth and her hair in the hopes that when he was finished she could slink out of his life in shame and regret. She wouldn’t pursue Pikachu anymore, nor would she work for Team Rocket. All she wanted as she knelt there with tears and spit masking her face was to forget she had ever seen Ash and his friends.

When the young man started to hit his peak, he did it with a cruelty that Jessie had fully come to expect from him. His cock locked down as deep as he could manage and his fingers interlocked at the back of her head, forcing her down until her nose ached against his lap and she screamed a gargled, muffled cry from the ache. With a few short grunts Ash began to cum straight down poor Jessie’s throat; his member throbbing while that tender chute of flesh bulged from the rush. A few squirts of cum straight down into her belly were a swift punishment but Ash was nowhere near done, and soon his cock was flooding her mouth to the point her cheeks puffed out and rushing her senses until it splurted from her nose in a disgraceful display. She cried out again in a moist scream while cum flooded her, and Ash’s cock finally broke free of her lips as she started to desperately cough and gag. As she spat his cream onto the grass below and shuddered with the heartache of her trial Ash just kept squirting; splashing cum over Jessie’s face, her smooth and lovely breasts, and most noticeably her hair. Those pretty red locks were streaked with white by the time Ash was complete, and the young man grinned as he moved his fingers out for the other side.

“Whew. Better clean my cock off before I fuck you.” Ash smiled to the trembling woman, his fingers moving into Jessie’s hair and scooping a handful of the few remaining clean threads. While Jessie continued to sob and tremble Ash openly wiped his cock off in her hair; smearing what was left of her spit and his cum into the silky red fabric and letting it fall back into place. A hearty laughed filled him and he stretched his arms out wide, his prick already bobbing back to full attention and ready for more. “All right! I’m feeling pretty good, slut! I can go one more round before I meet up with the others, so bend over and lift that ass. Spread your pussy out wide for me, and show me where I get to bury my cock next!”

“Y...You...I…” Jessie, with dark lines on her cheeks and cum still smeared across her face, was still at a complete and utter loss. She was typically a woman that always had a comment behind her teeth, but this time the only thing filling her mouth was the heady flavor of Ash’s cum. She pulled one gloved hand past her face to wipe away some of the cum oozing from her nose, and whimpered as she moved to do exactly as she was told. In utter obedience Jessie bent down on all fours on the grass and spread her knees out wide; even letting one hand slink underneath her body to the tender folds of her pussy. She spread herself wide just as she had been told, and spoke with a blushing, frightened tone. “...g...get it over with…”

Distracted by heartache and wearing thick gloves, Jessie hadn’t realized one critical thing about her pussy just yet. Namely...she was wetter than she had ever been.

That arousal certainly crept up on her when Ash locked himself into place behind her, kneeling on the grass and slapping his meaty cock right on top of her curvy ass. A few grinds of his hips helped to demonstrate just how deep he’d be going into her - uncomfortably deep, as it would seem. But it wasn’t until he lowered his shaft and pressed the tip against Jessie’s pussy did she realize a heat rushing through her, one that made her cheeks burst into a vibrant blush and made her quiver with a lust that she could only scarcely comprehend.

“Oh, and before you ask?” Ash smirked, and let his fingers once more sink into that long, tail-like trail of hair. It was just so convenient for fucking purposes! As he held on tight he leaned in close, and allowed his cock to ooze in a slow, steady few inches. “...I’m not pulling out. Sluts like you are meant to collect cum.”

And with that dark declaration, Ash fucked himself down to Jessie’s tender, frightened, but very wet core.

From the very first strike of cock into her fuckhole, Jessie was frightened by how her body reacted to it. Her eyes went wide and her teeth clenched, and she felt every muscle in her body tighten up. Suddenly those boots and gloves were as tight as a second skin across her body, and she could feel them riding across her flesh as goosebumps arose on every spot along her frame. Ash’s cock was so big that she could hardly handle it all, and when he drove in so hard his balls swung forward to slap against the sensitive, raw folds of her hood. Her clit shivered with pleasure and her pussy ached as it was stretched, and yet within the shameful display and the fact that Ash was helping himself...she had to admit, a dark, dark part of her liked it.

She kept her head down for the moment, trying to sort through her feelings as Ash started to fuck her. His cock drug in and out of the walls of her pussy, slathered in her arousal stolen without her consent, throbbing with the weight of his anger and frustration. Even though he had just unloaded in Jessie’s throat and across her hair he was just as hard as ever, and that member forced a tight seam with the tender, tight entrance of Jessie’s fuckhole. Her knees spread a little more as Ash began to press his weight into her, and he pulled back on the slut’s hair to force her face away from the ground so she could feel the sun on her smeared mascara and spit-stained features.

“I don’t hear you moaning, whore.” Ash hungrily growled as he thrust back and forth, plunging into her hole with a series of moist, audible thrusts. Every time he pounded inside Jessie’s senses flared with hunger, and Ash was making it sorely tempting for her to give in and allow herself the chance to verbalize her pleasure. He reached one hand around to squeeze viciously at one of Jessie’s large, cum and spit covered breasts, tweaking a nipple until the point it was sore within his fingers and making her quiver even more intensely. “Scream for me, slut. You never have any trouble screaming when Pikachu fries your worthless ass.”

“Y...You...how dare...how dare y.-ahhhh!” Jessie’s voice rose up into the air as Ash slapped her hard across the ass; so hard that it left that visible imprint across both of her cheeks. Afterwards he spread both hands against her rear and stretched it out, exposing the tight pucker of her ass and spitting squarely onto it. Though he had every intention of finishing inside her pussy, it didn’t hurt to press his thumb against that rear entrance to give her the threat that he might shift gears yet again. Jessie, whimpering and giving another tiny sob, looked over her shoulder with pleading, desperate eyes lined in runny black makeup. “Please...not there…”

“Then moan for me, bitch.” Ash repeated the command, and squeezed his thumb against her ass juuuust enough to make her squirm. “Let the whole forest know how much you like being used as a slutty cocksleeve.” He punctuated those words while he thrust deep into her, and when he finished his speech he started to pick up faster and faster. His hands moved from Jessie’s ass and locked firmly against her waist, slamming her back into him just as she launched forward. With one last promise he made Jessie a final threat; a certain promise if she didn’t obey him. “If you don’t start moaning, I swear I’ll wreck your ass, next!”

Jessie, with no other option, gave into the deepest, darkest desires burning inside of her. She hadn’t resisted moaning out of any semblance of shame or fear that others might hear them - she had held back because she deeply feared what her own body would do once she started. She was terrified that once she started moaning, once she gave into the pleasure of being used as Ash’s whore, that she might not be able to go back. That as soon as those words flowed from her lips they’d be impossible and unwilling to ever, ever return. Now that her hand was forced and her throat tightened with a swallow of aching emotion, she had no recourse but to look up to the sky and the warm, warm sun, and let filthy words flow from her tongue.

“Fuck...fuck me! Fuck your worthless slut!” She groaned, speaking past lips still flavored of Ash’s cock. “Fuck my dirty cunt, let me know I’m your cocksleeve! Ohh, it...it feels so good! My pussy’s so hot, your cock is so big, I’m...I’m going to cum! Your little fuckslave is going to cum on your big, hard, cooooooooock~”

Sure enough, as soon as she began it was impossible to stop, and it sure enough led her to a swift, violent climax. Ash had only asked her to moan, and yet her whorish desires in that moment had brought out something far, far darker. As her gloved fingers sank into the dirt and her leather-clad knees spread a little further Jessie had that intense orgasm she promised; her pussy clamping against Ash’s cock as she began a sudden torrent of depraved squirting. Her thighs twitched in erratic patterns and her nectar shot straight to the grass below them, hitting the leaves with her very own water type attack. As her nectar dashed to the ground and her desperate cries filled the air, her shame was followed by Ash’s triumphant laugh and another fierce slap to the side of her ass.

“Wow, you really know how to be a whore!” He grinned, his fingers sinking in against the soft curve of her rear and giving her a fierce squeeze. “I might just have to keep you around, bitch! Wouldn’t you like that?! Sucking on your new owner’s cock every morning? Making sure you don’t go to bed until I’ve gotten to fill each of your dirty holes with cum?!”

“Yes, yes, Master! Yes, Master, fuck me anywhere you want!” Jessie’s eyes were open and her pupils tiny; her body still quivering in the aftermath of her intense orgasm. Her throat ached with the volume of her screams, but yet they continued to dash over the trees and down the nearby stream. “Use your whore! Fuck her mouth, her cunt, her ass! Just...just fuck her, Master! Fuck her with your cooooooooooock…~”

Ash, a triumphant grin on his face, wasn’t quite done. He already had Jessie broken, and it hadn’t taken all that long. Just a few inches of thick and hungry cock and she was already swearing to be his loyal bitch. That wasn’t enough for Ash; though, not nearly enough for all the trouble she had caused. With a wide smile Ash’s hands left Jessie’s waist to sink both into her hair, and as he pulled back on it like a fierce leash his most dangerous words flowed out. He forced her to arch back; pulling on her so far that her hands left the ground and she was suspended by her knees and the tension yanking at her hair, those big, sloppy, glorious tits bouncing with each thrust. It was as he held his little fuckpig in such a prone, painful state that Ash spoke up once more and delighted in how she gripped his cock at the announcement.

“I’m not pulling out, bitch!” He laughed, his orgasm starting to rock through him. “And if I don’t knock you up this time, I’ll do it again, and again, and again! Hope you’re ready to get pregnant, whore!”

“Yes, yes, yes, Master! Yes, Master, breeeeeeeed meeeeeee~” Fully lost to the heat running through her, Jessie’s most primal impulses took over and bashed away the cocky personality that once lived inside of her. She didn’t even flinch at the announcement she was to be Ash’s breeding bitch - or rather, the only flinching she did was when her pussy shivered from the knowledge. All she wanted in that moment, with her mouth open and drooling and her tits flopping back and forth, was to be filled and bred by this dominant young man. Her eyes rolled back in her head and she felt one more orgasm rush over her at the knowledge; an orgasm that similarly filled her mind with visions of what her future was like.

A future with a big pregnant belly, following behind Ash and his friends while only wearing her gloves and boots. Maybe Ash would keep her on a leash? Maybe he would let his friends fuck her? It didn’t matter - she’d still be there to eagerly suck her master’s cock every morning and let him fuck all her holes at night. She’d cradle her pregnant belly to keep it safe if he wanted to fuck her doggy style, and she’d savor every bit of cum he shot down her throat or into her tight, wet cunt. She would follow him right into the middle of town as a naked whore that was willing to serve if he so demanded, for in that moment she was exactly that broken and claimed. Though Ash had forced himself inside of her, it was Jessie’s deepest, darkest fantasies that had made it possible for him to do so.

She was always a worthless cocksleeve...it had just taken Ash to prove it.

By the time her fantasy snapped back to reality and her climax had ended, she was already laying on the ground shivering from the aftermath. Her body was sore and trembling, her pussy was filled and overflowing with cum, and her throat ached from all of her depraved screaming. The only motion running through her save for the rapid breathing was a gentle swinging of her hair; the result of Ash once more using those red locks to clean off his cock. As the young man stood up and pulled his jeans up once more, he looked down to the naked, trembling, well-fucked bitch at her place at his heels. He spit once more; this time landing against her cheek where it slowly seeped over her lips. The gentle appearance of her tongue as it crept up to claim it was all he needed to see - even in that lusty aftermath, even as she gasped for breath and struggled to come to terms with everything, she was his.

“Good job, bitch. Nice to see you’re not completely worthless.” Ash finally chuckled, and gave a long, satisfied stretch. “Two minutes to rest, then I expect you to follow me. Take one second more, and you have to do it on your hands and knees.

“Y...Yes...Mas...Master…” Jessie whimpered, and her eyes stared off into the distance. It was the most intense, violent, and satisfying sex of her life...and she was completely beholden to it. The little twerp with the Pikachu was the last person she had ever expected as a master, and yet there she was, struggling to draw herself up to her feet and balance on wobbly, shaking knees.

She was a mess; covered in spit and tears and smeared mascara, cum covering the inside of her thighs, sweat making grass stick to her body in countless spots. Still, despite the messy bitch she was, her master wanted her to follow. With a tremble and a smile Jessie turned to pad after him, her voice hoarse, yet submissive and loyal.

“Master...Master, I’m ready…~” She called out in a sweet, song-like voice. “Thank you for fucking me, Master!”

As they walked, Ash merely smirked. He didn’t need a Pokeball to catch and train this whorish bitch.

The End.


	2. Three Cheers for Cock

**Summary for the Chapter:**

> Jessie's been nicely broken down to become Ash's whore - she's even started wearing a cheerleading outfit so she could support her favorite Pokemon Master/Sexual Master!

Ash’s Best Catch  
Chapter 2: Three Cheers for Cock  
-by Drace Domino

“Yay, Ash, go go go! He can’t lose, no no no!” Jessie cheered enthusiastically, waving her pom poms through the air and bouncing up and down with every step. She was cheering her master on from the sideline, watching as he won yet another Pokemon battle. When Ash’s opponent was defeated and he called his Gliscor back to its Pokeball, Jessie darted over to her master with a smile on her face and a spring in her step. “Wonderful battle, Master! You did great!”

Ash merely smirked, and rewarded his cheering section by giving her a slap - and grope - on her ass. After all, if Gary had cheerleaders follow him around, why shouldn’t Ash? Without a word the young man turned on a heel and set down along the road once more, leaving his opponent defeated and Jessie keeping up with him at a hurried pace.

It had been a month or so since Ash had first broken Jessie, fucking her into a wet mess and forcing her to learn to love his cock. Over the course of the past few weeks her infatuation with being Ash’s slut had only increased, and she hadn’t left his side for a moment. Her Team Rocket outfit had been completely discarded by now; left where Ash had stripped it away and thrown it into a river, and it was replaced now with a uniform that better fit her current role. A short cheerleading skirt and a midriff top that left her body mostly exposed was Jessie’s current attire of choice; complete with knee socks, sneakers, and bright frilly pom poms for her to wave about while her master battled. The uniform was clearly a few sizes too small for her which ensured her ample breasts were constantly stretching the fabric of her top, and that the skirt only barely covered her ass and pussy. No panties, of course - Ash’s prized slut didn’t have need for such things.

Ash tucked his hands into his pockets as he walked along the path, giving a small nod to other travelers in a polite fashion. To anyone else on the road he was just another Pokemon trainer with his older, unusual female friend who was pattering behind him with an adoring look in her eyes. Only when someone looked back at the pair after passing did they notice that Jessie’s bare ass was practically exposed by her short cheerleading skirt, and it offered the faintest hint of the true nature of their relationship. The red haired girl - whom at that point now wore her long hair in two frilly pigtails for proper cheering - was completely subservient to the younger man she travelled with. His slave, his servant, and most notably...his slut.

Ash veered off the road at a certain point; making a hard right and travelling into where the woods started to get a little more dense. It had been a long day on the road and it was well past time to start setting up camp, but the real reason he was stopping for the day was his desire to fuck his prized bitch. Seeing her bounce around during all of his battles had a natural reaction within his young body, and he was already throbbing, aching against the front of his pants. Once he stepped into the woods deep enough to find a private clearing Ash turned around on a heel, and looked at his pet with a confident, dominant smile.

“All right, whore, on your knees.” He barely even needed to say the words before Jessie was already there; throwing her bare knees into the dirt as she moved her hands for her master’s lap. She was already drooling as she started to work at his jeans and quickly unzipped him, eagerly slipping her hand forward so she could fish for his cock. Ash merely smirked, and tossed his backpack to the side as he got comfortable and prepared for his post-victory blowjob. “You’re hungrier than usual, cunt. Did you get off watching me battle?”

“Ohh, yes, Master!” Jessie swooned, and when she pulled Ash’s enormous cock free she fawned over it with desperation. For the moment she was content to stroke it sweetly back and forth, and she looked up at the young man’s face with admiring, even worshipping eyes. While she pressed his warm shaft to her cheek she spoke with a voice of pure delight and glee - she couldn’t be happier to be Ash’s slave. “It reminds me of when you made me yours. It was so wonderful being made your bitch!”

Ash grinned wide, and lowered a hand to grasp one of Jessie’s ponytails. He guided her towards the front of his lap and pressed his tip to her mouth, easily shoving forward and sliding his cock past her lips. As the warm wetness of Jessie’s mouth wrapped around the first few inches of his cock Ash gave another joyful sigh, and stretched out while he trusted her to tend to his member. One long month he had been enjoying this kind of pleasure - blowjobs whenever he demanded them throughout the day, starting with the one that Jessie gave him every morning. Her pussy and her ass whenever he desired, and she wouldn’t even hesitate before bending over. He had made his broken bitch into a desperate and wanton whore, and it was the perfect place for a girl that had caused him so much trouble in the past.

“I wonder how many people have seen your pussy today, slut.” Ash smirked, watching as Jessie worked so tirelessly to cover his cock in spit. “That skirt isn’t nearly big enough. Every time you cheer for me you’re showing your fuckhole to everybody.” A soft chuckle rose from him, and he pushed his length deeper into her mouth to suggest he wasn’t looking for an answer. Her mouth wasn’t for conversation - it was for sucking cock. “Everyone knows what a whore you are, Jessie. Everyone knows that you’re only good for making your master cum.”

Jessie, her face by now smeared with spit resting across a heady blush, wasn’t even about to argue. Her knees dug in against the dirt and she sucked Ash’s cock down with a few more deep sucks; pressing her nose into his lap and accommodating his girth all the way down her throat. Over the past few weeks she had learned how to deepthroat her master, though no amount of practice would ever make it completely comfortable to handle such a massive prick. Her throat bulged and her eyes watered as she held herself down; forcing that deepthroat to prove her loyalty and love for the man that had broken her. When she pulled her mouth back and let Ash’s cocktip go past her lips with a pop she instantly started to cough, but it wasn’t long before she was right back to work, smearing Ash’s spit-covered prick all over her pretty face.

“I love my Master’s cum.” Jessie whispered in response to Ash’s words, and stuck her tongue out as her mouth opened wide. She slapped herself back and forth with Ash’s prick, striking herself so hard in the face with that heavy piece of cockmeat that a few wet slapping noises filled the air around them. She lowered her hand to the edge of her cheerleader skirt to pull the frill up and expose her pussy; a glistening mess that by now had painted her own thighs with clear, sweet squirt. “My pussy’s wet, Master...will you fuck me, please? Fuck your slave?”

Ash, always savoring his cruel streak when Jessie begged, held off on an answer for now. He merely smirked and arched an eye to show his slave he was considering it, and after a few moments he gestured to his dripping shaft and spoke in a patient, thoughtful voice.

“Let’s see how well you suck my cock, first.” He proposed his lover a challenge, one with high stakes indeed. “If you do a good job and show me what a whore you are, I’ll fuck your pussy afterwards. Do you think you can be even more of a slut for me, Jessie?” 

“Ohh, yes, Master!” Jessie giggled in enthusiastic delight, and went immediately to work. The knowledge that if she sucked her master’s cock well enough that she’d get a reward was profound motivation, for nothing could make Jessie’s body shiver with energy and excitement quite so much as the promise of Ash fucking her raw and deep. She went right back to deepthroating her master with a zealous glee, and as she did so she filled the nearby area with the sound of her wet, messy cocksucking. Sloppy noises surrounded them as did the fragmented gurgling of a woman fucking her own throat against a massive prick, and as she bobbed back and forth she made a spit-covered mess of her pretty cheerleading blouse. Ash simply shuddered in pleasure and reared back on his heels, and his hands lowered down to the most natural place for him to grab her: her pigtails.

“Not good enough, slut.” Ash whispered, just as his hands tightened against Jessie’s pigtails. “Let me show you how to use your fuckhole!” And with that, he threw his strength into the already violent and wild blowjob. With Ash’s hands on Jessie’s pigtails the young woman’s sloppy deepthroating session went even more berserk, all of her wet noises intensifying as she choked on his cock and let it bulge her throat. Her eyes rolled back in her head and her hands fell from Ash’s lap, hanging limp in the dirt below as she became little more than a wet cheerleading hole for him to fuck his cock into. The same mouth that had boasted of Ash’s battle prowess mere moments ago was now used to satisfy much more than the young man’s ego; and Jessie’s lips were spread wide so she could offer this glorious service to her master.

Ash didn’t take long to cum - there was no reason to hold back when he could use his bitch whenever he liked. Before he did; however, he pulled his prick away from Jessie’s mouth and suddenly reached down to pull something from the side of his backpack. His canteen was quickly uncorked as he held his shaft in one hand, and he pointed that throbbing tip to the open mouth of the empty drinking tool.

“Fffuuuuuck…” Ash hissed through his teeth as he unloaded; firing squirt after squirt of his cum into his canteen. Jessie was only just now coming back to her senses with a sore throat and a sloppy face; blinking as she saw her master use his cum on something other than her. Ash’s cock was throbbing and spewing his cream in sudden bursts, unleashing rope after rope straight into the mouth of his canteen until it was heavy from his release. Only when he was finished did he pull the thing away from his prick, and toss it to Jessie with a smirk. “Eat your dinner, cunt. Then you can have some more cock.”

Jessie, cradling the heavy canteen, licked her lips and nodded. She was still kneeling in the dirt in her full cheerleading outfit, but by now she already looked like a complete mess. Her hair was dishevelled, her knees were dirty, and her pretty face was a mess of spit, tears, and most notably - pleasure. She looked at her master with the same adoring eyes, and spoke just before bringing the canteen up to her lips.

“Thank you for dinner, Master.” She cooed. “It’s my favorite…” And with that, the depraved whore tipped the mouth of the canteen to her lips and started to drink. Ash watched with depraved glee as his slave chugged down the canteen filled with his cum, studying how her throat bulged with every gulp and how she made sure to slide a finger forward to catch anything that oozed out. Jessie tilted her whole head back as she drank, and she didn’t come up for air until she had drained the canteen of nearly every drop. When she finished slurping and gulping down all of her master’s cum she looked back at him once more, opening her mouth wide to show she had swallowed every bit. “All gone, Master! Can I have some more cock now?!”

“Hmph...well...since you behaved.” Ash remarked simply, and pointed to Jessie’s spot in the dirt. “Hands and knees, whore. Lift that skirt up so I can see how wet you are.”

Jessie practically giggled as she obliged, dropping down to her hands and knees and lifting her skirt up over her ass. She spread her knees apart in the dirt and lifted her rear up as much as she was able, making sure that anyone passing by could get a nice, long look at her exposed ass and her tender, wet pussy. Ash stepped behind his pet and sized her up for a few seconds, merely to build the tension with great delight. When he finally knelt down behind her and slid a hand forward to test her pussy; however, Jessie howled like a desperate whore.

“So fucking wet…” Ash marvelled, his fingers left soaked by his pet’s hot, hungry hole. He moved his hand forward to wipe those fingers off on Jessie’s face, which naturally only made his hand stickier and wetter. What a sloppy slut she was! “Try not to scream too loud tonight, whore. Remember how embarrassed you were last time.” It had just been a few days ago that Jessie’s cries had brought the attention of another couple - one that had stopped and stared completely dumbstruck as Ash fucked his whore in front of them.

“Oh, y-yes, Master...please…” Jessie was rocking back and forth now, like a horny animal caught in the midst of heat. She rolled her hips from side to side and even smeared her master’s cock with her lips, but wasn’t so bold as to put him inside of her. That was something only her master was allowed to bestow. “Please fuck your whore...your slave...please use her as your toy…” Ash, the wicked smile on his face a stark departure from the innocent young man he used to be, simply nodded and thrust forward.

Jessie’s pussy spread easily for the massive size of Ash’s length, and he drilled her right down to the hilt on the very first thrust. Despite Jessie’s promise to behave she screamed in glee from the very beginning, her hands tightening on the dirt below her and her knees spreading even more. If it wasn’t for the fact that Ash reached out to claim the handlebars of her pigtails once more, she likely would’ve been face-first in the dirt as a moaning, sticky mess. As it was her tongue rolled out past her lips and she drooled to the ground below, all amidst a series of desperate cries while her pussy was stretched and fucked.

“Yes, Master, it’s so big! Fuck me, Master! Fuck your dirty whore!” She was loud - so loud that they might as well had not even gone into the woods. Surely along the road people could hear, and they’d likely know that it was the slutty cheerleader they had seen earlier getting fucked like a depraved bitch. Jessie thrashed and spasmed as Ash fucked her steadily, his cock slipping in and out of her with remarkable, intense ease. Pleasure overwhelmed them both, and Jessie had a few twitching orgasms long before Ash was ready. How could she resist? The thrill of having her slutty fuckhole claimed so viciously when complimented with the warm feeling of a belly full of cum? It was her idea of paradise now that she had been broken down into the position of a depraved, slutty cunt.

“So tight!” Ash grunted, truly amazed that his whore had managed to stay so tight with her daily ruttings by his impressive length. Every time he fucked her it surprised him what a wonderful ride he got from his bitch, ensuring that he made the right choice in picking Jessie as his slave. As his hands tightened on her pigtails and his motions quickened considerably, the young man’s body tensed up harder as his cock slammed deep into her hole. “I’m going to fill you up with cum, cunt! What do you say?”

“T...Thank you, Master! Thank you for giving me all your cum!” Jessie wailed, her smile desperate and wide and her eyes streaming with joyful tears. There was nothing she wanted more in the world in that moment to be filled with her master’s cum, to feel it ooze inside of her pussy and saturate her walls. Ash had always fucked her raw and without any trace of protection, and he never hesitated to fill her up with more cum than she ever knew a single man could produce. The thrill of it only intoxicated her further, and she knew that by now she simply had to be pregnant. How could she not be? She was her master’s cocksleeve several times a day, and relished in the feel of having her pussy flooded with his cream. “Cum...cum...cummmm…!”

Jessie spasmed in an orgasm that drug Ash into his own, and before long the cheerleader was a twitching, shivering mass as she squirted and screamed while she was filled with cum. Ash hilted himself deep into her depraved hole as he drained his cock of cum, squirting deep into Jessie’s nethers and shuddering violently as he did so. When he pulled back once more a heavy trail of it oozed out of Jessie’s slit, and it wiggled back and forth when he spanked her ass with a hard strike. The little cheerleader collapsed down into the dirt; breathing heavy and oozing cum from her well-fucked pussy, but wearing a smile past her messy cheeks and her sweat-covered visage. Ash, only now tucking his cock back in, merely grinned as he gestured to the east of the clearing.

“I saw a stream not that far away. Go clean up, and wash out my canteen.” Ash’s orders were simple, and they came complemented with the thud of his canteen hitting the dirt a few inches from Jessie’s face. “And what do you say if someone sees what a mess you are?”

Jessie, lifting herself up from the dirt and showing herself off to be a spit-covered, cum-dripping mess, reached for her pom poms and gave them a tiny shake.

“Yay Ash, go go go~” She responded weakly, but sweetly, and with a messy smile on her face. She stood up tall, with cum oozing from her pussy like a tiny white waterfall between her legs. “I’m his whore, woah woah woah~”

End of Part Two.

**Author's Note:**

> Rough! Sloppy! Hard! Dat just happens to be what Jessie likes.
> 
> [Check me on tumblr for more smuts!](http://dracedomino.tumblr.com)


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